Duplicate Remote Password

Question

For over a week, an employee has noticed that the system prompts him to enter his password a second time after he has already logged in. He usually closes the second prompt because when he tries to enter his password again, he receives an error message.

This issue does not affect all employees for example, I work in IT and have not experienced this problem myself

Answer 1

Hi Adalid Bori,

From the looks of that error message, the "Sign in again" prompt is almost certainly being triggered by a specific Sign-in frequency setting within your Conditional Access policies.

I’d suggest heading into the Microsoft Entra admin center under the Protection tab to check if a session policy is being applied too aggressively to that user’s specific group. If the cloud settings appear correct, the issue is usually just a stale or corrupted local authentication token, so having the employee clear their Windows Credential Manager and then re-authenticating through the "Access work or school" section in the system settings should resolve the loop.

It is likely just a mismatch between the device's local session and the tenant's policy requirements rather than a broader system failure.

Here’s the link to the Microsoft Learn documentation for managing session lifetimes. It covers exactly how to configure the sign-in frequency in Entra ID, which should help you resolve that repetitive prompt issue. I’d recommend checking the "Periodic reauthentication" settings first, as that's the most likely culprit for this kind of behavior: https://learn.microsoft.com/en-us/entra/identity/conditional-access/howto-conditional-access-session-lifetime

Best regards,

Tracy.

Answer 2

Hi Adalid Bori,

I wanted to follow up and see if you were able to resolve that "Duplicate Remote Password" prompt after checking the Conditional Access policies and clearing the Credential Manager. Did those steps fix the issue for your employee, or are you still seeing that second login prompt?

If the information I provided was helpful and solved the problem, please click "Accept Answer". This helps other IT professionals in the community find this solution more easily when they encounter similar authentication loops.

Let me know if you need any more help with Entra ID or device registration!

Best regards,

Tracy.